US3766122A

US3766122A - Polyisobutylene oxide compositions

Info

Publication number: US3766122A
Application number: US00273373A
Authority: US
Inventors: H Sawada; K Ohata; N Tsukane
Original assignee: Daicel Corp
Current assignee: Daicel Corp
Priority date: 1971-08-21
Filing date: 1972-07-20
Publication date: 1973-10-16
Anticipated expiration: 1990-10-16
Also published as: GB1364392A; DE2236468A1; FR2152561A1; FR2152561B1; JPS4829848A; JPS5115543B2

Abstract

POLYISOBUTYLENE OXIDE COMPOSITIONS CONTAINIING 1-20 WT. PERCENT, BASED ON POLYISOBUTYLENE OXIDE, OF AN A-OLEFIN OXIDE OR MIXTURE OF TWO OR MORE A-OLEFIN OXIDES OF THE GENERAL FORMULA:

O<(-CH2-C(-R)(-R'')-)

WHEREIN EACH OF R AND R'' REPRESENTS HYDROGEN OR A STRAIGHT CHAIN, SATURATED ALKYL GROUP, WITH THE SUM OF THE CARBON ATOMS IN R PLUS R'', BEING IN THE RANGE OF FROM 14 TO 40.

Description

United States Patent 01 hee- ,7bb,l22 Patented Oct. 16, 1973 3,766,122 POLYISOBUTYLENE OXIDE COMPOSITIONS Hideo Sawada, Keichi Ohata, and Nagayoshi Tsukane, Saitama, Japan, assignors to Daicel Ltd., Osaka, Japan N Drawing. Filed July 20, 1972, Ser. No. 273,373

group consisting of ethyl, butyl, hexyl, octyl, deeyl, dodecyl, tetradecyl, hexadecyl, octadecyl, eicosyl, docosyl, tetracosyl and hexacosyl groups, the sum of the carbon atoms in R plus R being 1440.

The purpose of the present invention cannot be attained Clalms pnonty ggj gg gg 1971 5 by using a-olefin oxides in which the sum of the carbon Int CL cosg 43/00 atoms in R plus R is 13 or less carbon atoms inclusive, CL 2 0 .30 4 R 1 Cl i or 41 or more carbon atoms inclusive, because the former has high volatility and the latter has poor compatibility 1 with polyisobutylene oxide. ABSTRACT OF THE DISCLOSURE Polyisobutylene oxide in the present invention is a Polyisobutylene oxide compositions containing 1-20 Wt. crystalline polymer of a high degree of polymerization obpercent, based on polyisobutylene oxide, of an a-olefin tained by polymerizing isobutylene oxide in the presence oxide or mixture of two or more a-olefin oxides of the of, for example, an organozinc compound. general formula: 5 The compositions of the present invention may contain R conventional amounts of additives, such as pigments, stabilizers or other fillers, depending upon the purpose of the resin compositions.

R O The compositions of the present invention have various wherein each f R and represents hydrogen a advantages such as negligible volatility, stability against straight chain, saturated alkyl group, with the sum of the light and h as W as high mold rfileasmg P p carbon atoms in R plus being in the range f fro 14 from molding mach1nes. The a-olefin oxldes do not harm to 0 the transparency of the resin, they have excellent compatibility with the resin and they render unnecessary use BACKGROUND OF THE INVENTION Of lubricant in the resin composition.

The a-olefin oxides of the present invention can be Fleld of the lnventlon mixed easily with polyisobutylene oxide by usual means The present invention relates to plasticized, soft polysuch s a blender, mixer. kneader and rolls- For e p isobutylene oxide compositions of an excellent impact mlXlng can be efiected 3 F T01l mah1ne a strength obtained by incorporating an Ot-Olfifi oxide in Su table kneader or by d1ssolving or dispersing an et-olefin polyisobutylenfi oxide oxide in a suitable solvent, whlch solvent can be removed readily, and mixing the solution or dispersion with poly- Descnptlon of the Pnor art isobutylene oxide powder or pellets and then removing Conventional polyisobutylene oxide is a useful polymer the S t. having excellent mechanical strength and high crystal- As described above, by using the polyisobutylene oxide u i b t h polymer l h th disadvantages of poor compositions of the present invention, the impact strength, softness and flexibility and insufficient impact strength. softnesds and fiexiblillity of pollyiscgautyline olxifcile can b; increase owing to e particu ar e ect o a-o e n oxide av- SUMMARY OF THE INVENTION ing the structure shown by the above general formula, We have found that softness, flexibility and impact without deterioration of the other desirable properties of strength can be imparted to polyisobutylene oxide by inpolyisobutylene oxide. In addition, polyisobutylene oxide corporating in it about 1-20 parts by weight, per parts moldings with excellent stability can be obtained easily by weight of polyisobutylene oxide, of an wolefin oxide without reduction in viscosity due to heat treatment. Thus, or a mixture of two or more flt-Olefil'l oxides of the general the compositions of the present invention are greatly formula: 4.5 valuable from the viewpoint of industrial uses.

R The present invention will be illustrated by way of the following illustrative example. The reduced viscosities in the example were determined R 0 with an Ubbelohdes viscometer at C. in o-dichlorowherein each f R and represents hydrogen or a 50 benzene solution (concentration: 0.1 g./ 100 cc.). straight chain, saturated alkyl group, with the sum of the carbon atoms in R plus R being in the range of 14 to 40. EXAMPLE As a-olefin oxides used in the present invention, there Alpha-olefin oxides shown in Table 1 were mixed with maybe mentioned, for example, 1,2-epoxyhexadecane, 1,2- polyisobutylene oxide powder (reduced viscosity=3.5) epoxyheptadecane, 1,2 epoxyoctadecane, 1,2-epoxyn0na- 55 ith a roll at C. for 5 minutes, decane, 1,2 epoxyheneicosane, 1,2-epoxydocosane, 1,2- The resulting compositions were heat-pressed at a temepoxytricosane, 1,2-epoxypentacosane, 1,2-epoxyhexacosperature of C. under a pressure of 100-140 kg./cm. ane and 1,2-epoxynonacosane. As compounds of the above to obtain sheet samples about 1 mm. in thickness, general formula wherein both R and R represent alkyl The resulting sheets were soft and the tensile elongagroups, there may be mentioned a compound or mixture 60 tion and the falling-ball impact strength thereof were of compounds in which R and R are members of the superior to those of sheets containing no a-olefin oxide.

TABLE 1 Cone. of

olefin oxide Falling-ball in polymer Tensile impact wt. strength Tensile strength Run No. Olefin oxide percent) (kg/cm?) elongation (kg-cm.) 1 (control) N0ne. r 0 400 20 4.5 2 a-Olefin oxide of 20-28 carbon atoms 1 395 30 7. 5 3 o I 5 395 45 10.5 4 a do 10 390 60 12.0 5 a-0lefin oxide of 3040 carbon atoms 5 390 30 12. 0 6 a-Olefin oxide of 1416 carbon atoms 5 395 30 7. 5

of polyisobutylene oxide containing from 1 to 20 percent 5 by weight, based on the weight of polyisobutylene oxide, of one or more a-olefin oxides of the formula wherein R and R is hydrogen or straight chain saturated alkyl, and the sum of the carbon atoms in R plus R is in the range of from 14 to 40.

4 References Cited UNITED STATES PATENTS 3,062,755 11/1962 Hill et a1. 2602 3,354,097 11/1967 Vandenberg 2602 3,509,074 4/1970 Kamio 2602 HAROLD D. ANDERSON, Primary Examiner 10 E. A. NIELSEN, Assistant Examiner US. Cl. X.R. 2602 A, 33.8 EP